Without bringing up the lease again and aggravate him even more as he wanted to talk to his attorney (according to what he said/presented he is a kid with rich parents with attorney), what some other ways to minimize the situation (ensuring no random security issue / damages on house and car), get my garage and driveway back, and get him to leave peacefully as soon as possible?

And you cannot purchase property from yourself to complete a 1031 exchange.If the LLC files as a partnership and files it's own returns the that LLC is the tax payer for the property and not you the member. 

We made an aggressive offer and secured the land.

I think in might add more job security and bring more people to that location but again, those are not the hi-paying jobs like it would be the case of amazon HQ2. 

I've had many LTR's where after a year I have to repaint the entire home, replace appliances and do other repairs that easily exceed the security deposit. 

. ($500K if you're married and filing jointly.)

But after this incident we informed the tenant the dog had to be secured at all times. 

I figured I would appear as a low risk to a lender, but I've been shocked by crazy stuff before, so part of me was concerned.After doing some more research, it looks like I need to look into a "secured loan". 

ie. paperwork, loan documents, securities, or other agreements. 

Maybe @John Underwood knows this, but when you file your taxes at the end of the year, should we calling out the VRBO service fee that they charge to the owner as a deductible expense?